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C0483

Sigma-Aldrich

Z-Leu-Leu-Glu-7-amido-4-methylcoumarin

≥95%, solid

Synonym(s):

Cbz-Leu-Leu-Glu-AMC, Z-LLE-AMC

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About This Item

Empirical Formula (Hill Notation):
C35H44N4O9
Molecular Weight:
664.75
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥95%

form

solid

solubility

DMSO: soluble

storage temp.

−20°C

SMILES string

CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)Nc2ccc3C(C)=CC(=O)Oc3c2

InChI

1S/C35H44N4O9/c1-20(2)15-27(38-34(45)28(16-21(3)4)39-35(46)47-19-23-9-7-6-8-10-23)33(44)37-26(13-14-30(40)41)32(43)36-24-11-12-25-22(5)17-31(42)48-29(25)18-24/h6-12,17-18,20-21,26-28H,13-16,19H2,1-5H3,(H,36,43)(H,37,44)(H,38,45)(H,39,46)(H,40,41)/t26-,27-,28-/m0/s1

InChI key

FOYHOBVZPWIGJM-KCHLEUMXSA-N

Amino Acid Sequence

Z-Leu-Leu-Glu-AMC

General description

Z-Leu-Leu-Glu-7-amido-4-methylcoumarin is a fluoropeptide. It acts as a substrate for caspase-like activity.

Application

Z-Leu-Leu-Glu-7-amido-4-methylcoumarin has been used as a fluorogenic substrate for peptidyl glutamyl peptide hydrolase (PGPH) in rat soleus muscle, neonatal cardiomyocytes and rat brain samples.

Biochem/physiol Actions

Fluorogenic substrate for the measurement of the peptidylglutamyl-peptide hydrolyzing activity of the 20S proteasome.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M Orlowski et al.
Biochemistry, 32(6), 1563-1572 (1993-02-16)
Initial studies on the specificity of the multicatalytic proteinase complex (MPC; EC 3.4.99.46) led to the identification of three distinct proteolytic components designated as trypsin-like, chymotrypsin-like, and peptidylglutamyl-peptide hydrolyzing, all sensitive to inactivation by 3,4-dichloroisocoumarin (DCI), a general serine proteinase
P Berthon et al.
Pflugers Archiv : European journal of physiology, 454(4), 625-633 (2007-03-06)
In the present study, we determined the impact of 5 and 10 days of muscle deconditioning induced by hindlimb suspension (HS) on the ubiquitin-proteasome system of protein degradation and caspase enzyme activities in rat soleus muscles. A second goal was
Aimee D Husom et al.
Archives of biochemistry and biophysics, 421(1), 67-76 (2003-12-18)
Myofibrillar protein degradation is mediated through the ubiquitin-proteasome pathway. To investigate if altered proteasome activity plays a role in age-related muscle atrophy, we examined muscle size and proteasome function in young and aged F344BN rats. Significant age-related muscle atrophy was
Caterina Branca et al.
Neurobiology of aging, 35(12), 2726-2735 (2014-07-19)
Currently, there are no available approaches to cure or slow down the progression of Alzheimer's disease (AD), which is characterized by the accumulation of extracellular amyloid-β (Aβ) deposits and intraneuronal tangles that comprised hyperphosphorylated tau. The β2 adrenergic receptors (β2ARs)
Salyan Bhattarai et al.
Journal of autoimmunity, 75, 118-129 (2016-08-16)
Idiopathic inflammatory myopathies (IIMs) are diseases with muscle weakness, morphologically characterized by inflammatory infiltration and increased expression of MHC class I molecule on myofibers. Immunoproteasome, as a proteolytic complex that shapes the repertoire of antigenic peptides, has been previously demonstrated

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